US3702823A - Fluorosilicone lubricants containing 2-nitromesitylene - Google Patents
Fluorosilicone lubricants containing 2-nitromesitylene Download PDFInfo
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- US3702823A US3702823A US167036A US3702823DA US3702823A US 3702823 A US3702823 A US 3702823A US 167036 A US167036 A US 167036A US 3702823D A US3702823D A US 3702823DA US 3702823 A US3702823 A US 3702823A
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- US
- United States
- Prior art keywords
- steel
- nitromesitylene
- fluorosilicone
- radicals
- weight percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000314 lubricant Substances 0.000 title abstract description 12
- SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical group CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 title abstract description 9
- 229910052782 aluminium Inorganic materials 0.000 abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 7
- 229910001369 Brass Inorganic materials 0.000 abstract description 5
- 239000010951 brass Substances 0.000 abstract description 5
- -1 alkyl radicals Chemical class 0.000 description 53
- 229910000831 Steel Inorganic materials 0.000 description 17
- 239000010959 steel Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000000654 additive Substances 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- 239000012530 fluid Substances 0.000 description 9
- 235000010210 aluminium Nutrition 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 5
- 231100000241 scar Toxicity 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229920005560 fluorosilicone rubber Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/102—Silicates
- C10M2201/103—Clays; Mica; Zeolites
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/10—Compounds containing silicon
- C10M2201/105—Silica
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/062—Polytetrafluoroethylene [PTFE]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/20—Containing nitrogen-to-oxygen bonds
- C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- This invention relates to improved fiuoroalkylpolysiloxanes which contain minor amounts of Z-nitromesitylene.
- the invention relates to fluorosilicone fluids exhibiting enhanced antiwear characteristics and superior thermal stability.
- Organopolysiloxane fluids are known lubricants.
- Dimethylpolysiloxanes are general lubricants but have poor antiwear characteristics whenused to lubricate steel on steel sliding surfaces.
- Fluorosilicones, such as trifluoropropylmethylpolysiloxanes are much better lubricants for steel on steel but exhibit poor lubrication for steel on brass and steel on aluminum.
- the fluorosilicone fluids find only limited use in environments requiring lubrication of metal surfaces other than steel on steel.
- organosilicon compositions comprising of (a) 98 to 99.8 weight percent of an organopolysilxane fluid containing at least 30 mol percent units in which R; is a perfluoroalkylethyl radical of from 3 to 12 carbon atoms, and R is selected from the group consisting of lower alkyl radicals and the phenyl radical; any remaining units being of the formula R' SiO or in which R' is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.2 to 2 weight percent 2- nitromesitylene.
- organopolysilxane fluid containing at least 30 mol percent units in which R; is a perfluoroalkylethyl radical of from 3 to 12 carbon atoms, and R is selected from the group consisting of lower alkyl radicals and the phenyl radical; any remaining units being of the formula R' SiO or in which R' is selected from the group consisting of monovalent hydrocarbon radical
- R can be any perfluoroalkylethyl radical of no more than 12 carbon atoms, such as and the like.
- R can be any lower alkyl radical containing from 1 to 6 inclusive carbon atoms, such as methyl, propyl, isopropyl, butyl and hexyl. R can also be a phenyl radical.
- R can be any monovalent hydrocarbon radicals, such as alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, neopentyl, hexyl, octyl, dodecyl, octadecyl, 3 methylheptyl, 6 butyloctadecyl, tertiary butyl, myricyl and 2,2-diethylpentyl; alkenyl radicals such as, vinyl, allyl, hexenyl, butenyl, 3-octeny1, 4,9- octadecadienyl and 4-nonenyl; alkynyl radicals such as propynyl, heptynyl, butynyl, decynyl; alkenynyl radicals such as 1-penten-3-ynyl, 2-ethyl-l-
- R' monovalent halohydrocarbon radicals, such as 'aliphatic groups such as chloromethyl, 3-chloropropyl, 3,3,3-trichloropropyl, perfiuorovinyl, chlorooctadecyl or radicals of the formula R CH CH where R, can be any perfluoroalkyl group such as trifluoromethyl, perfluoroethyl, perfluoroisobutyl, perfluoroheptyl or perfluorooctadecyl; aromatic groups such as dichlorophenyl, tetrabromoxenyl, tetrachlorophenyl, alpha,alpha,alpha-trifluorotolyl or iodonaphthy]; cycloaliphatic groups such as chlorocyclohexyl, bromocyclopentyl or chlorocyclohexenyl and aralkyl groups such as chlorobenz
- the preferred monovalent hydrocarbon and halohydrocarbon radicals are those having no more than 18 carbon atoms.
- R groups are lower alkyl radicals, the phenyl radical and Z-phenylpropyl radicals.
- fiuoroalkylpolysiloxanes are fluids, generally having viscosity in the range of 20 to 20,000 cs. and include copolymers such as and the like.
- Particularly preferred fluids are the triorganosilyl endblocked 3,3,3 trifluoropropylmethylpolysiloxanes having a viscosity in the range of about 20 to 1000 cs. when measured at 77 F.
- the 2-nitromesitylene additive is a known compound and is commercially available from a number of sources.
- the compound can be depicted as CH; CH:
- the lubricating compositions of the invention may optionally contain corrosion inhibitors, extreme pressure agents, anti-oxidants, dyes and the like.
- the invention also contemplates the use of thickening agents in combination with the compositions to formulate improved greases.
- Thickening agents suitable for use in such a grease formulation include fatty acid soaps, carbon blacks, silica, clay, polytetrafluoroethylene and the like.
- the thickener should not be one that is reactive with the 2- nitromesitylene additive.
- the thickening agent will generally be present in an amount from about 10 to 60 weight percent of the grease compositions.
- the 2-nitromestitylene increases the ther mal stability of the fluid.
- the weight loss at elevated temperatures of additive-containing fluids is significantly decreased. Because of this thermal stability, the compositions of the invention have utility as base stocks in fluorosilicone rubber formulations.
- the lubricity characteristics were determined by means of the 4-Ball test.
- the 4-Ball tests were conducted on a Roxanna wear testing machine wherein a /2 inch diameter steel ball is rotated against three lubricated stationary /2 inch metal balls under various conditions and loads. After testing, the length and width of the scar on each stationary ball is measured and the average of the six measurements is taken as the wear scar diameter. The smaller the wear scar, of course, the better the lubricant.
- EXAMPLE 2 A fluorosilicone composition similar to that of Example 1 except that it contained only 0.5 weight nitromesitylene was tested as a lubricant for steel on alumi num. The wear scar after A: hour at 167 F., 1200 r.p.m. and 10 kg. load was 0.50 mm., showing that the additive is eifective at low concentrations.
- EXAMPLE 3 Sufiicient Z-nitromesitylene was mixed with trimethylsilyl-endblocked fluorosilicone copolymer (60 mole percent CH SiO units and 40 mol percent CF CH CH (CH SiO units) having a viscosity of 288 cs. to form a composition containing 1.5 weight percent of the additive.
- the wear scar for steel on aluminum under the conditions of Example 2 was 2.1 mm., demonstrating that the additive is effective with copolymeric fluorosilicones.
- a composition consisting essentially of 98 to 99.8 weight percent of an organopolysiloxane fluid containing at least 30 mol percent units in which R, is a perfluoroalkylethyl radical of from 3 to 12 inclusive carbon atoms, and R is selected from the group consisting of alkyl radicals of no more than 6 carbon atoms and the phenyl radical; any remaining units being of the formula R' SiO or RESPO- in which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and 0.2 to 2 weight percent of 2- nitromesitylene.
- composition of claim 1 wherein the organopolysiloxane is triorganosilyl-endblocked 3,3,3-trifiuoropropylmethylpolysiloxane having a viscosity of from 20 to 1000 centistokes at 77 F.
- composition of claim 1 where the organopolysiloxane is trimethylsilyl-endblocked 3,3,3-trifluoropropylmethylpolysiloxane.
- composition of claim 3 wherein the 2-nitromesitylene is present in an amount in the range of from 0.5 to 1.5 weight percent.
- a lubricant comprising the composition of claim 1 containing sufficient thickening agent to form a grease.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
MINOR AMOUNTS OF 2-NITROMESITYLENE ARE ADDED TO FLUOROSILICONE LUBRICANTS TO IMPROVE THE STEEL ON BRASS AND STEEL ON ALUMINUM ANTI-WEAR CHARACTERISTCS.
Description
United States Patent US. Cl. 252-496 6 Claims ABSTRACT OF THE DISCLOSURE Minor amounts of 2-nitromesitylene are added to fluorosilicone lubricants to improve the steel on brass and steel on aluminum anti-wear characteristics.
This invention relates to improved fiuoroalkylpolysiloxanes which contain minor amounts of Z-nitromesitylene. In one aspect the invention relates to fluorosilicone fluids exhibiting enhanced antiwear characteristics and superior thermal stability.
Organopolysiloxane fluids are known lubricants. Dimethylpolysiloxanes are general lubricants but have poor antiwear characteristics whenused to lubricate steel on steel sliding surfaces. Fluorosilicones, such as trifluoropropylmethylpolysiloxanes are much better lubricants for steel on steel but exhibit poor lubrication for steel on brass and steel on aluminum. Thus, the fluorosilicone fluids find only limited use in environments requiring lubrication of metal surfaces other than steel on steel.
By the practice of the present invention, the antiwear characteristics of fluorosilicones on steel on brass and steel on aluminum are greatly enhanced and the thermal stability is increased, thus rendering them suitable for high temperature lubrication of various metals.
In accordance with the invention, there are provided improved organosilicon compositions comprising of (a) 98 to 99.8 weight percent of an organopolysilxane fluid containing at least 30 mol percent units in which R; is a perfluoroalkylethyl radical of from 3 to 12 carbon atoms, and R is selected from the group consisting of lower alkyl radicals and the phenyl radical; any remaining units being of the formula R' SiO or in which R' is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and (b) 0.2 to 2 weight percent 2- nitromesitylene.
As described above, R can be any perfluoroalkylethyl radical of no more than 12 carbon atoms, such as and the like.
R can be any lower alkyl radical containing from 1 to 6 inclusive carbon atoms, such as methyl, propyl, isopropyl, butyl and hexyl. R can also be a phenyl radical.
R can be any monovalent hydrocarbon radicals, such as alkyl radicals such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, isopentyl, neopentyl, hexyl, octyl, dodecyl, octadecyl, 3 methylheptyl, 6 butyloctadecyl, tertiary butyl, myricyl and 2,2-diethylpentyl; alkenyl radicals such as, vinyl, allyl, hexenyl, butenyl, 3-octeny1, 4,9- octadecadienyl and 4-nonenyl; alkynyl radicals such as propynyl, heptynyl, butynyl, decynyl; alkenynyl radicals such as 1-penten-3-ynyl, 2-ethyl-l-buten-3-ynyl; cycloaliphatic radicals such as, cyclobutyl, cyclopentyl, cyclo- 3,702,823 Patented Nov. 14, 1972 hexyl, cycloheptyl, propylcyclohexyl, 2,4 dimethylcyclopentyl, cyclohexenyl, bicyclo-[3.1.0]hexyl, tricyclo- [3.2.1.1- ]-5-nonenyl, spiro[4.5]decyl, dispiro[4.1.4.2]- l-tridecenyl, decahydronaphthyl, 2,3-dihydroindyl and 1,2,3,4-tetrahydronaphthyl; aryl radicals such as phenyl, tolyl, xylyl, 3-ethylphenyl, xenyl, naphthyl, anthracyl, pentacenyl, 3,4-methylethylphenyl, 9,9'-bifluoryl and 4-mterphenyl; and aralkyl radicals such as 2-phenyl-octyl, S-methyl 2 (4-isopropylphenyl)heptyl, benzyl, Z-ethyltolyl, 2 ethyl p cymyl, diphenylrnethyl, 4,5 diphenylpentyl, Z-phenylethyl and 2-phenylpropyl.
Also included within the scope of R' are monovalent halohydrocarbon radicals, such as 'aliphatic groups such as chloromethyl, 3-chloropropyl, 3,3,3-trichloropropyl, perfiuorovinyl, chlorooctadecyl or radicals of the formula R CH CH where R, can be any perfluoroalkyl group such as trifluoromethyl, perfluoroethyl, perfluoroisobutyl, perfluoroheptyl or perfluorooctadecyl; aromatic groups such as dichlorophenyl, tetrabromoxenyl, tetrachlorophenyl, alpha,alpha,alpha-trifluorotolyl or iodonaphthy]; cycloaliphatic groups such as chlorocyclohexyl, bromocyclopentyl or chlorocyclohexenyl and aralkyl groups such as chlorobenzyl, beta-(ch1orophenyl)ethyl or beta- (iodophenyl)ethyl or beta- (bromophenyl)propyl.
The preferred monovalent hydrocarbon and halohydrocarbon radicals are those having no more than 18 carbon atoms. Especially preferred as R groups are lower alkyl radicals, the phenyl radical and Z-phenylpropyl radicals.
The above-described fiuoroalkylpolysiloxanes are fluids, generally having viscosity in the range of 20 to 20,000 cs. and include copolymers such as and the like.
Particularly preferred fluids are the triorganosilyl endblocked 3,3,3 trifluoropropylmethylpolysiloxanes having a viscosity in the range of about 20 to 1000 cs. when measured at 77 F.
7 The 2-nitromesitylene additive is a known compound and is commercially available from a number of sources. The compound can be depicted as CH; CH:
Only minor amounts of the additive, from 0.2 to 2 weight percent, preferably from 0.5 to 1.5 weight percent, are necessary to obtain the desired degree of lubricity. The optimum amount will depend upon the nature of the fluorosilicone and its application. Amounts greater than two weight percent can be used, but are generally uneconomical. W
Other additives can be utilized in the above compositions without departing from scope of the invention. Thus, the lubricating compositions of the invention may optionally contain corrosion inhibitors, extreme pressure agents, anti-oxidants, dyes and the like. The invention also contemplates the use of thickening agents in combination with the compositions to formulate improved greases. Thickening agents suitable for use in such a grease formulation include fatty acid soaps, carbon blacks, silica, clay, polytetrafluoroethylene and the like. The thickener should not be one that is reactive with the 2- nitromesitylene additive. The thickening agent will generally be present in an amount from about 10 to 60 weight percent of the grease compositions.
In addition to enhancing the antiwear properties of fluorosilicones, the 2-nitromestitylene increases the ther mal stability of the fluid. The weight loss at elevated temperatures of additive-containing fluids is significantly decreased. Because of this thermal stability, the compositions of the invention have utility as base stocks in fluorosilicone rubber formulations.
The following examples are illustrative and not intended to be limiting of the present invention which is delineated in the claims. In the examples, the lubricity characteristics were determined by means of the 4-Ball test. The 4-Ball tests were conducted on a Roxanna wear testing machine wherein a /2 inch diameter steel ball is rotated against three lubricated stationary /2 inch metal balls under various conditions and loads. After testing, the length and width of the scar on each stationary ball is measured and the average of the six measurements is taken as the wear scar diameter. The smaller the wear scar, of course, the better the lubricant.
EXAMPLE 1 Suflicient 2-nitromesityle'ne was mixed with trimethylsilyl endblocked 3,3,3 trifiuoropropylmethylpolysiloxane (300 cs.) to form a fluorosilicone composition containing 1.5 weight percent of the additive. The antiwear properties and thermal stability of this composition were compared to the properties of the pure polymer. Results are given below:
These data demonstrate the eifect of the additive on the steel on brass and steel on aluminum lubrication properties of fiuorosilicones. The additive also reduces the weight loss of fluorosilicones at elevated temperature. These effects are quite unexpected since they were not observed in other silicone lubricants, such as polydimethylsiloxane.
EXAMPLE 2 A fluorosilicone composition similar to that of Example 1 except that it contained only 0.5 weight nitromesitylene was tested as a lubricant for steel on alumi num. The wear scar after A: hour at 167 F., 1200 r.p.m. and 10 kg. load was 0.50 mm., showing that the additive is eifective at low concentrations.
EXAMPLE 3 Sufiicient Z-nitromesitylene was mixed with trimethylsilyl-endblocked fluorosilicone copolymer (60 mole percent CH SiO units and 40 mol percent CF CH CH (CH SiO units) having a viscosity of 288 cs. to form a composition containing 1.5 weight percent of the additive. The wear scar for steel on aluminum under the conditions of Example 2 was 2.1 mm., demonstrating that the additive is effective with copolymeric fluorosilicones.
That which is claimed is:
1. A composition consisting essentially of 98 to 99.8 weight percent of an organopolysiloxane fluid containing at least 30 mol percent units in which R, is a perfluoroalkylethyl radical of from 3 to 12 inclusive carbon atoms, and R is selected from the group consisting of alkyl radicals of no more than 6 carbon atoms and the phenyl radical; any remaining units being of the formula R' SiO or RESPO- in which R is selected from the group consisting of monovalent hydrocarbon radicals and monovalent halohydrocarbon radicals; and 0.2 to 2 weight percent of 2- nitromesitylene.
2. The composition of claim 1 wherein the organopolysiloxane is triorganosilyl-endblocked 3,3,3-trifiuoropropylmethylpolysiloxane having a viscosity of from 20 to 1000 centistokes at 77 F.
3. The composition of claim 1 where the organopolysiloxane is trimethylsilyl-endblocked 3,3,3-trifluoropropylmethylpolysiloxane.
4. The composition of claim 3 wherein the 2-nitromesitylene is present in an amount in the range of from 0.5 to 1.5 weight percent.
5. A lubricant comprising the composition of claim 1 containing sufficient thickening agent to form a grease.
6. The lubricant of claim 5 wherein the thickening agent is present in an amount in the range of from 10 to 60 weight percent, based on the total weight of lubricant.
References Cited UNITED STATES PATENTS 3,629,106 12/1971 Quaal et al. 25249.6 X
DANIEL E. WYMAN, Primary Examiner W. I. SHINE, Assistant Examiner U.S. Cl. X.R. 252-515 R, 403
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16703671A | 1971-07-28 | 1971-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3702823A true US3702823A (en) | 1972-11-14 |
Family
ID=22605683
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US167036A Expired - Lifetime US3702823A (en) | 1971-07-28 | 1971-07-28 | Fluorosilicone lubricants containing 2-nitromesitylene |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3702823A (en) |
| CA (1) | CA965404A (en) |
| DE (1) | DE2237262A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5217633A (en) * | 1988-06-25 | 1993-06-08 | Bayer Aktiengesellschaft | Low-temperature lubricating oil |
| EP0613941A3 (en) * | 1993-03-03 | 1994-09-21 | Dow Corning Toray Silicone | Fluorosilicone lubricant compositions. |
| CN105814179A (en) * | 2013-11-20 | 2016-07-27 | 道康宁公司 | Organosiloxane compositions |
| US12290433B2 (en) | 2019-04-05 | 2025-05-06 | Forsight Vision6, Inc. | Fluorosilicone copolymers |
-
1971
- 1971-07-28 US US167036A patent/US3702823A/en not_active Expired - Lifetime
-
1972
- 1972-04-06 CA CA139,045A patent/CA965404A/en not_active Expired
- 1972-07-28 DE DE2237262A patent/DE2237262A1/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5217633A (en) * | 1988-06-25 | 1993-06-08 | Bayer Aktiengesellschaft | Low-temperature lubricating oil |
| EP0613941A3 (en) * | 1993-03-03 | 1994-09-21 | Dow Corning Toray Silicone | Fluorosilicone lubricant compositions. |
| US5445751A (en) * | 1993-03-03 | 1995-08-29 | Dow Corning Toray Silicon Co., Ltd. | Fluorosilicone lubricant compositions |
| CN105814179A (en) * | 2013-11-20 | 2016-07-27 | 道康宁公司 | Organosiloxane compositions |
| US20160281019A1 (en) * | 2013-11-20 | 2016-09-29 | Dow Corning Corporation | Organosiloxane compositions |
| US10011801B2 (en) * | 2013-11-20 | 2018-07-03 | Dow Silicones Corporation | Organosiloxane compositions |
| US20180291299A1 (en) * | 2013-11-20 | 2018-10-11 | Dow Silicones Corporation | Organosiloxane compositions |
| CN105814179B (en) * | 2013-11-20 | 2019-11-05 | 美国陶氏有机硅公司 | Organosiloxane composition |
| US12290433B2 (en) | 2019-04-05 | 2025-05-06 | Forsight Vision6, Inc. | Fluorosilicone copolymers |
Also Published As
| Publication number | Publication date |
|---|---|
| CA965404A (en) | 1975-04-01 |
| DE2237262A1 (en) | 1973-02-08 |
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